In 1995, James Jessiman released a DOS based modeling program called LDraw. It was designed specifically to model creations built with LEGO bricks and other LEGO pieces. LEdit, a parts editor based on the LDraw format was initially released with only 3 parts; a 2x2 Brick, a 2x3 Brick, and a 2x4 Brick. Both of these programs were command line driven.

In 1996, two minifigs named Jill and Gary started the MFWT, or MiniFig World Tour, being mailed from AFOL to AFOL. The tour included the idea that the minifigs would interact with different MOCs. LDraw was offered as an option for these people to add instructions for their MOCs to a "community idea book". The same year LeoCAD, the first LDraw editor for the Windows platform, was released by Leonardo Zide.

In 1997, Steve Bliss released a program called LDraw Add-On; a program used to easily control command lines and files for LDraw. This would be the first of many programs authored that would build on the LDraw system. It is considered a system because James spent as much time designing the file format for parts and models as the program itself. The parts file format was flexible, extensible, and designed to be an open system. The initial work done by James to outline the system made everything that we do with the tools today possible. Without the foresight of James, we would not be able to build the complex layouts, nor would we have such a wide variety of add-ons and compatible tools.
Unfortunately, on July 25, 1997, James passed away due to complications from the flu. He was only 26 years old. James had made several good friends and they created a memorial for him and vowed to continue the work he had started. Two more programs were released that year; Jacob Sparre Anderson's Fractal Landscape Editor, and Lutz Uhlmann's LDraw to POVRay conversion tool (L2P). Terry Keller started the James Jessiman memorial site, and both Terry and Steve Bliss started managing the LDraw parts library, allowing the community to continue to participate in the expansion of LDraw.

1998 saw the release of Bram Lambrecht's LDraw and LEdit tutorial, as well as Lars Hassing's L3P converter, which allows LDraw files to be converted to PovRay using all of the parts included in the LDraw parts library. Towards the end of the year LDraw and L-CAD discussion move to lugnet.cad, a news server with focus newsgroups for different LEGO-related subjects, started by Todd Lehman and Suzanne Rich.

The official website of everything LDraw was released on July 7, 1999. www.LDraw.org was started by Tim Courtney after several months of discussion and has remained the predominant resource for LEGO CAD software, discussions, and community interaction. Also in 1999, Michael Lachmann introduced MLCad, a Windows' based LDraw editor. It has grown since that time to be the most widely used Windows based LDraw model editor and is currently on version 3.20.

By the year 2000, Tim Courtney, Bram Lambrecht, Lars Hassing and others are presenting LDraw at various different venues, and the popularity of the program and the work by the community is increasing dramatically. It is a year for viewers: Lars Hassing releases L3Lab while Travis Cobbs publishes LDView with realtime 3D rendering using OpenGL.

Earlier in the year of 2001 several LDraw organizers and program authors meet with LEGO Direct to discuss virtual LEGO topics. In July of 2001, the legacy of James Jessiman was solidified at BrickFest, when James' parents (Don and Robyn) traveled from Australia to give the first annual "James Jessiman Memorial" award to honor an individual who has contributed to the furthering of LDraw, the DAT format, and James' memory . It was awarded to Steve Bliss. On the other side of the Atlantic Jaco Van Der Molen demonstrates LDraw at LEGOWORLD 2001, a LEGO fan event in Zwolle, Netherlands. This event draws crowds of over 27,500 people.

The LDraw Standards Committee (LSC) was formed in 2002. This committee insured that good standards existed and were followed for parts libraries, file formats, and other crucial parts of LDraw.

2003 saw the release of the first 2 books published on how to use LDraw and several accompanying tools. The books "LEGO Software Power Tools" and "Virtual LEGO" were released in January and July respectively. As part of the process of writing the book "LEGO Software Power Tools", Kevin Clague designed and wrote a new authoring tool called LPub. Later releases of the tool have become an integral part of the suite and are used extensively as an easy way of turning LDraw model designs into instructions by creating all of the different assembly steps automatically. Tim Courtney presented the LDraw suite of tools to SIGGRAPH. By the year 2003, the programs and tools designed around the work of James had become so popular and had so many users and proponents, that the name actually was being misused and misunderstood. Because of this, the LDraw.org staff released an official statement declaring that all programs and tools that support the file format started by James should be referred to as the "LDraw System of Tools". This is because LDraw has come to represent much more than the original DOS executable, it now embodies the system for mathematically describing LEGO elements and models; a system originally designed by a man from Australia. A man who might not have lived to see the difference he made, but who undoubtedly changed the way AFOLs around the world would use their computers. The James Jessiman Memorial Award is given to Jacob Sparre Andersen. And last but not least on September 6, the website was relaunched using a new CMS after the site moved to the Peeron.com servers earlier in the year.

The fifth year of LDraw.org, was a busy time for the LDraw community, with events such as: Ratification of the LDraw.org Bylaws on February 26, 2004 turning the loose group of devoted people into an official organization. Election of the first LDraw Steering Committee (SteerCo), formalizing the LDraw.org Contributors Agreement (CA) and the election of the second LSC. In software, there were the following releases: MLCad V3.10 - with support for LSynth (an extension that generated hoses and tubing), LDraw Design Pad v1.5.6, LDView Version 2.1, LD4DModeler 1.1 and the release of 4 LDraw Part Updates with a total of 977 parts files. Also in 2004 Chris Dee, with assistance from Martyn Boogaarts, ran the LDraw booth at LEGOWorld in the Netherlands, and Orion Pobursky ran a LEGO CAD Developer Roundtable at SIGGRAPH, with Tim Courtney presenting an "Intro to Free 3D LEGO Modeling Software." For his contributions to the LDraw community the 2004 James Jessiman Memorial Award was presented to Lars C. Hassing. Another achievement is LDraw shown on G4TechTV Screen Savers.

Throughout the year of 2005 the administration tried to contact past and present part authors to get them to sign the Contributor Agreement for the switch to a new license scheme. The CA-library not only became redistributable but also allowed to combine the original library authored by James Jessiman with all updates published so far to make one easy download. At the end of the year almost 150 authors had signed the CA while 22 couldn't be traced, leaving the community with more than 100 parts in the need of rewriting because of the non-compliant copyright. The last official part library update under the old license was published on December 28 - there won't be any new updates for more than two years. An important step away from the old DOS-convention set by the original LDraw-program was a change in the policy regarding the subfiling of dithered colors and thoughts about an internationalisation of the part library. Also in 2005 Willy Tschager assisted by Jaco Van Der Molen ran the LDraw booth at LEGOWorld, while Allen Smith released Bricksmith 1.0 an LDraw editor for Mac. Furthermore it saw the release of: Txt2Dat, LPub 2.4, LDraw Design Pad 1.5.7 and MLCad 3.2 by Michael Lachmann, who was presented with the 2005 James Jessiman Memorial Award.

In 2006 part authors started re-writing part not compliant to the new license, while the LSC revised the part specification to support the Contributor Agreement and to lift the 1.0.0 proposal for the LDraw File Format to version 1.0, which included for example meta statements, BFC or a new header standard, allowing much better use of the library by third-part tools, since they could rely on a defined metadata structure. Furthermore the rules and boundaries for the LSC were ratified in the LSC Final Draft. This year also brought shifts in administration with the appointment of Willy Tschager and Tim Gould as webmasters and Ross Crawford as third Parts Tracker admin. 2006 also saw the releases of LDView 3.1 as the first LDraw-based tool to support automatically downloading unofficial parts from the LDraw.org Parts Tracker, LeoCad 0.75 or DATHeader 1.01 a program written by Michael Heidemann to generate or edit CA-complaint part headers. The James Jessiman Memorial Award was presented to Orion Pobursky.

Sadly also 2007 didn't see a LDraw Parts Update as the task to adjust the parts header to the new specs and license turned out to be more tedious than expected, since the process couldn't be automated and more than 3500 files had to be edited individually by the Parts Tracker Admin Chris Dee. On the plus side the LSC officially formalized version 1.0 of the LDraw File Format specification which included also the ratification of several documents related to it. The webmasters launch RACHAL - the RAytracing CHALlenge and added the POTM - Part Of The Month to LDraw's relaunched contests, set up a tribute picture gallery to commemorate the 10th anniversary of James Jessiman's passing and had the pleasure to add a link to his rediscovered original website. The annual election of the SteerCo brought a European shift with two members from USA and Australia and three from old Europa. After 2 years of negotiation the Lego Universe team started to share information regarding the brick shapes. In 2007 also a good bunch of programs were released like LD4DStudio a new animation software by Roland Melkert; version 1.0 of IseCalc, Coverer and Isecalc by Philo or a new editor for Windows, SR3D Builder by Sergio Reano. Finally the JJMA, the James Jessiman Memorial Award was presented to Kevin Clague.

2011 saw the migration to a new forum and the JJMA was awarded to Travis Cobbs.

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